Breakout: Jon Hamm

How does a man this handsome—and this talented—hide in Hollywood for a decade? John Hamm's long, tortured journey into the (klieg) light

The 1920s Mediterranean-style house that Jon Hamm shares with longtime girlfriend Jennifer Westfeldt does, in fact, sit on a hill—an honest-to-goodness, nonmetaphorical geologic elevation that looks out over the neighborhood of Los Feliz and east toward the expanses of lesser Los Angeles beyond. Still, on a sunny morning when Hamm has agreed to take me on a tour of the homes he has occupied since arriving in L.A., it's hard not to see it through a haze of myth: the end point in a story that—not unlike Mad Men, the show that's made Hamm famous—is part American Fairy Tale, part American Gothic.

So bring out the capitals: Call it the House on the Hill.

Leaning up against the front door is a cardboard FedEx box addressed to Westfeldt and containing a dress for the actress to wear, a few days later, at the Emmys, where Mad Men will win basic cable's first-ever Best Drama award. "I've been trying on dresses all week," Westfeldt apologizes, upon opening the door. Blond, slim, and flustered, she drags the box inside with one hand while holding off Cora, an energetic pit bull–shepherd mix, with the other. She cocks her head upstairs, mock-aggrieved. "Meanwhile, he just throws on a tux and looks great, you know?"

Well, actually, yes, we'd noticed. If you know one thing about Hamm, it's likely that, as Mad Men's Don Draper, he occupies a suit with the physical genius of Michael Phelps sliding into water.

Today, though, he descends the stairs wearing plaid shorts, a white linen shirt, and soccer sneakers. Hamm unsuited is kind of a frat guy, every inch the rabid sports fan and former high school football star. He says things like "Dude" and "Sweet" and "Dude, sweet!" On his head is a St. Louis Browns cap (facing frontward, thank the Lord). He looks like the kind of guy who is physically compelled to put on shorts the moment the temperature tops fifty-five degrees, a diagnosis he cheerfully confirms. Credit the totemic power of a suit, but he looks a full ten years younger than Don Draper, with about half the weight on his shoulders. How it is that the actor manages to make his '60s adman so much more than just another perfect design element on Mad Men's gorgeously curated set is not yet clear.

"This is going to be great," he says of our planned itinerary, a looping route through a city that he's embraced as perhaps only a midwesterner can. "One: You're going to get to see a shitload of L.A." He pauses, grins giddily. "Two: I have an awesome car."

The ride is a sleek, brand-new 2009 Audi S4—its exterior and interior going by the downright Draperific names Meteor Gray and Magma Red, respectively. Hamm bought the car only after getting the green light from his business manager. "He said, ‘I spend my days trying to restrain guys from buying Ferraris when they score a onetime guest shot on According to Jim. I think you're going to be fine,' " Hamm says. It probably helped ease the man's mind that Hamm had also just finished shooting his part as the heavy in the Keanu Reeves eco-sci-fi blockbuster The Day the Earth Stood Still. "It's the first car I've ever had that wasn't ‘responsible,' "he adds, accelerating onto the I-5. The freeway is uncharacteristically free of traffic. But then, it's been that kind of year.

Our first stop: a modest, English-cottage-style bungalow in the neighborhood known as West Los Angeles. This is where Hamm's aunt and uncle lived back in 1995, when Hamm arrived on Thanksgiving weekend. Everything he owned was in a beat-up ten-year-old Corolla. In the rearview mirror was St. Louis.

The Gateway City in the '70s and '80s was a declining urban center surrounded by white-flight suburbs. Hamm's family's fortunes seemed to mirror the place perfectly. His mother, Deborah, had moved to St. Louisfrom a small town in Kansas at 18 years old to find work as a secretary. She met and married an older widower who already had two daughters. Dan Hamm's family business, Daniel Hamm Drayage Co., had once provided horses to drag goods from laden barges up the banks of the Missouri River, there to be distributed all across the country. By the time Dan took over, shipping advances had long since diminished St. Louis's role as any kind of real gateway. He sold his once quintessentially American business and looked for work in the economy that replaced it: He peddled cars for a while. He dabbled in advertising.

When Hamm was 2, his parents divorced. He lived with his mother and saw his father on weekends, sometimes tagging along to joints like Al Baker's Restaurant, where Dan—nicknamed the Whale for his six-foot-three, 300-pound frame and outsize personality—would conduct business while Jon played under the piano. At home, Deborah was devoted to giving her only son a well-rounded, active education.

It was, in fact, on a trip to the St. Louis Art Museum that she disappeared into the bathroom and didn't come out for a long time. Hamm, then 10, had to ask a stranger to go in and check on his mother. Not long after, he came home from school to find his father waiting with the news that Deborah was in the hospital. Doctors had removed her cancer-stricken colon along with two feet of intestine, but it was obvious the malignancy had spread much further. "From then on, it was just pain management and deathwatch," Hamm says.